US2597497A - Purification of crude phenolacetone mixtures - Google Patents

Purification of crude phenolacetone mixtures Download PDF

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US2597497A
US2597497A US105650A US10565049A US2597497A US 2597497 A US2597497 A US 2597497A US 105650 A US105650 A US 105650A US 10565049 A US10565049 A US 10565049A US 2597497 A US2597497 A US 2597497A
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phenol
aqueous
acetone
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distillation
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George G Joris
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Allied Corp
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Allied Chemical and Dye Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/685—Processes comprising at least two steps in series

Definitions

  • This invention relates to purification of crude mixtures of acetone and phenol, in particular mixtures obtained by decomposition of cumene hydroperoxide.
  • acetone and phenol may be separated in commercially pure form from mixtures containing them by a process which comprises a distillation in the presence of water in which distillation acetone comes off overhead; water extraction of the residue, diluted with aromatic hydrocarbon, at elevated temperatures, with formation of an organic layer and an aqueous phenol layer; neutralization of the phenol in the organic layer thus produced and separation of aqueous phenol salt solution from said organic layer; extraction of the previously mentioned aqueous phenol layer with an aromatic solvent removing non-phenolic organic impurities therefrom; extraction of thus purified aqueous phenol with hydrocarbon solvent; and distillation of organic extract thus resulting, with removal of hydrocarbon solvent and separation of phenol from residue.
  • an aromatic hydrocarbon diluent e. g. unoxidized cumene present to the extent of about 50% by weight in the crude cumene hydroperoxide decomposition mixture containing phenol, acetone, and impurities.
  • the aromatic hydrocarbon diluent is used in this step to remove non-phenolic impurities and to promote separation of organic and aqueous layers.
  • Principal by-products in crude cumene hydroperoxide decomposition mixtures include acetophenone and dimethyl phenyl carbinol, both of which have densities close to that of aqueous phenol.
  • the presence of hydrocarbon diluent of lower density results in readier separation of organic layer from the aqueous phenolic layer.
  • Use of an aromatic rather than aliphatic-hydrocarbon as the diluent is important since it favors separation of the aromatic non-phenolic byproducts in the organic layer and phenol in the aqueous layer. Most satisfactory results are obtained when aromatic hydrocarbon diluent is at least 30% by weight of the crude phenolic distillation residue.
  • Elevated temperatures preferably at least about C., contribute to more rapid phase separation. Furthermore, use of elevated rather than room temperatures results in more favorable partition coefiicients of phenol in water versus phenol in the organic layer.
  • the organic layer from extraction tower 8 is passed via line 9 and valve II to a neutralizing tank nd separator I2.
  • tank Hi the organic layer is contacted with sodium hydroxide solution which extracts phenol remaining in this layer by converting the phenol to an aqueous solution of sodium phenate.
  • This aqueous sodium phenate is withdrawn mixture.
  • sodium hydroxide solution is regenerated by action oimilk of lime introduced through line 22 and valve 23. Calcium carbonate sludge is discharged from the causticizer via line 24 and valve 26. Regenerated sodium hydroxide solution is circulated via line 21 and valve 28 to neutralizing tank I2. Makeup sodium hydroxide solution of desired strength is introduced as needed via line 29 and valve 31.
  • the organic layer from neutralizing tank 12 is introduced via line 32 and valve 33 to still 34, wherein it is steam distilled.
  • a water-hydrocarbon azeotrope is taken off overhead at about 95 C. and is condensed in condenser and separator 36.
  • An organic product layer is withdrawn via line 31 and valve 38 and the aqueous layer is returned to the still via line 39.
  • Makeup steam or water for the distillation is introduced into the still as required via line 42 and valve 4 I.
  • the overhead organic products consist principally of the aromatic hydrocarbon diluent, e. g. cumene, and alpha-methyl styrene which is a by-product of cumene hydroperoxide decomposition.
  • the residue withdrawn from still 34 contains acetophenone and dimethyl phenyl carbinol.
  • aqueous phenolic layer containing about of phenol is withdrawn from extraction tower 8 via line 46 and valve 41.
  • This aqueous phenol contains small amounts of dimethyl phenyl carbinol and acetophenone impurities. It is countercurrently contacted in extraction tower 48 with about 2.5% by weight of aromatic hydrocarbon solvent, most suitably cumene. The cumene removes the above-noted impurities and a small amount of phenol.
  • the cumene layer is withdrawn from the top of extraction tower 48 and passed via line 49 and valve 5
  • the aqueous phenolic layer is withdrawn from extraction tower 48 via line 52 and valve 53, and is introduced into extraction tower 54 for removal of phenol.
  • extraction tower 54 the aqueous phenol. is countercurrently contacted with a hydrocarbon solvent, suitably benzene.
  • the benzene layer which contains about 5 or 6% by weight of phenol, is withdrawn from. the top of tower 54 via line 56 and valve 51 and is passed to still 65.
  • the aqueous layer from tower 54 containing about 1% phenol, is recirculated via line 58 and valve 59 to extraction tower 8 where,
  • hydrocarbon solvent e. g. benzene
  • condenser B3 the condensed in condenser B3.
  • the condensate is separated into a reflux ward flow stream which is returned to extraction tower 54 via line 66 and valve 61.
  • Make-up hydrocarbon solvent is introduced to extraction tower 54 via line 68 and valve 69.
  • the phenolic residue from still passes via line H and valve 12 to still 13 wherein phenol is separated overhead.
  • the phenol is condensed in condenser 15 and separated into a product stream, withdrawn via line 14 and valve 16, and. a reflux stream returning to the still via line 11. Bottoms may be withdrawn from still 13 when desired via line 18 and valve 19.
  • Commercially pure phenol is recovered in yields of better than of the phenol originally present in the crude decomposition product.
  • a process for separating acetone and phenol from a cumene hydroperoxide decomposition mixture containing them which comprises distilling said mixture in presence of water and taking oii acetone overhead; extracting with Water at elevated temperatures of at least about 85 C.
  • phenolic residue of said distillation which residue contains in addition to phenol at least 30% by weight of cumene, with formation of an organic layer and an aqueous phenol layer; neutralizing phenol in the organic layerthus produced and separating aqueous phenol salt solution from said organic layer; extracting from the aforementioned aqueous phenol layer, with cumene solvent, non-phenolic organic impurities therein and combining the organic layer from said extraction with the aforesaid acetone distillation residue; extracting thus purified aqueous phenol with hydrocarbon solvent; separating from organic-extract, thus resulting, hydrocarbon solvent and phenol and recycling aqueous layer, from said extraction of purified phenol, for the aqueous extraction of distillation residue from the acetone distillation step and for providing water in said distillation step.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented May 20, 1952 PURIFICATION OF CRUDE PHENOL- ACETONE MIXTURES George G. J oris, Convent, N. J assignor to Allied Chemical & Dye Corporation, New York, N. Y., a corporation of New York Application July 19, 1949, Serial No. 105,650
3 Claims.
This invention relates to purification of crude mixtures of acetone and phenol, in particular mixtures obtained by decomposition of cumene hydroperoxide.
The principal objects of the invention are to obtain acetone and phenol in commercially pure form, with minimum losses. Other objects and advantages will appear hereinafter.
I have found that acetone and phenol may be separated in commercially pure form from mixtures containing them by a process which comprises a distillation in the presence of water in which distillation acetone comes off overhead; water extraction of the residue, diluted with aromatic hydrocarbon, at elevated temperatures, with formation of an organic layer and an aqueous phenol layer; neutralization of the phenol in the organic layer thus produced and separation of aqueous phenol salt solution from said organic layer; extraction of the previously mentioned aqueous phenol layer with an aromatic solvent removing non-phenolic organic impurities therefrom; extraction of thus purified aqueous phenol with hydrocarbon solvent; and distillation of organic extract thus resulting, with removal of hydrocarbon solvent and separation of phenol from residue.
The accompanying drawing is a diagrammatic flow sheet illustrating one specific embodiment of my process. By way of illustration but not limitation of my invention, my process will now be described with reference to the drawing.
Separation of acetone Into still I is fed neutral crude phenol-acetone mixture, obtained by decomposition of cumene hydroperoxide, and water to bring the water content of the distilland to about by weight on the organic decomposition mixture introduced. Distillate is taken off overhead at about 56 C. and is condensed in condenser 2. A product stream, which is spectroscopically pure acetone, is withdrawn via line 3 and reflux is returned to the still via line 4. The overall recovery of acetone is better than 95%, and no phenol is lost during the distillation.
Use of water in this distillation step is important to assist in obtaining practically complete recovery of acetone without loss of phenol in the distillate. When a like distillation is performed in absence of water at atmospheric pressure, acetone remains in the residue even when the still temperature reaches 110l20 C. It might be expected, since phenol and water form an azeotrope boiling at 99.5 C., that presence of water would intensify the difficulty of separating acetone and phenol; but in fact the contrary is true.
Moreover use of water reduces formation of Tar formation in presence of water is remarkably less than that found in vacuum distillations at like still temperatures in absence of water.
Separation of phenol from non-phenolic aromatic organic constituents Crude phenolic residue containing nonphenolic aromatic materials is withdrawn from still I via pipe 6 and valve 1 and is passed to extraction tower 8. In the extraction tower this crude phenol is countercurrently contacted with water at temperatures of about 85-90 C. The crude phenol contains a, considerable proportion,
suitably about by weight, of an aromatic hydrocarbon diluent, e. g. unoxidized cumene present to the extent of about 50% by weight in the crude cumene hydroperoxide decomposition mixture containing phenol, acetone, and impurities.
The aromatic hydrocarbon diluent is used in this step to remove non-phenolic impurities and to promote separation of organic and aqueous layers. Principal by-products in crude cumene hydroperoxide decomposition mixtures include acetophenone and dimethyl phenyl carbinol, both of which have densities close to that of aqueous phenol. The presence of hydrocarbon diluent of lower density results in readier separation of organic layer from the aqueous phenolic layer. Use of an aromatic rather than aliphatic-hydrocarbon as the diluent is important since it favors separation of the aromatic non-phenolic byproducts in the organic layer and phenol in the aqueous layer. Most satisfactory results are obtained when aromatic hydrocarbon diluent is at least 30% by weight of the crude phenolic distillation residue.
Elevated temperatures, preferably at least about C., contribute to more rapid phase separation. Furthermore, use of elevated rather than room temperatures results in more favorable partition coefiicients of phenol in water versus phenol in the organic layer.
Recovery of non-phenolic aromatic constituents The organic layer from extraction tower 8 is passed via line 9 and valve II to a neutralizing tank nd separator I2. In tank Hi the organic layer is contacted with sodium hydroxide solution which extracts phenol remaining in this layer by converting the phenol to an aqueous solution of sodium phenate.
This aqueous sodium phenate is withdrawn mixture.
from the bottom of tank I2 via line 13 and valve I4 and is passed to a carbonating tank 16 wherein the sodium phenate is contacted with carbon dioxide gas bubbled in via line ll. The carbon dioxide reacts with the sodium phenate to form phenol and an aqueous solution of sodium carbonate and sodium bicarbonate. The phenol layer is withdrawn and the sodium carbonate and bicarbonate solution is taken off via line 18 and valve I9 to causticizer 2|.
In the causticizer sodium hydroxide solution is regenerated by action oimilk of lime introduced through line 22 and valve 23. Calcium carbonate sludge is discharged from the causticizer via line 24 and valve 26. Regenerated sodium hydroxide solution is circulated via line 21 and valve 28 to neutralizing tank I2. Makeup sodium hydroxide solution of desired strength is introduced as needed via line 29 and valve 31.
The organic layer from neutralizing tank 12 is introduced via line 32 and valve 33 to still 34, wherein it is steam distilled. A water-hydrocarbon azeotrope is taken off overhead at about 95 C. and is condensed in condenser and separator 36. An organic product layer is withdrawn via line 31 and valve 38 and the aqueous layer is returned to the still via line 39. Makeup steam or water for the distillation is introduced into the still as required via line 42 and valve 4 I. The overhead organic products consist principally of the aromatic hydrocarbon diluent, e. g. cumene, and alpha-methyl styrene which is a by-product of cumene hydroperoxide decomposition.
The residue withdrawn from still 34 contains acetophenone and dimethyl phenyl carbinol.
Purification of aqueous phenol Aqueous phenolic layer containing about of phenol is withdrawn from extraction tower 8 via line 46 and valve 41.. This aqueous phenol contains small amounts of dimethyl phenyl carbinol and acetophenone impurities. It is countercurrently contacted in extraction tower 48 with about 2.5% by weight of aromatic hydrocarbon solvent, most suitably cumene. The cumene removes the above-noted impurities and a small amount of phenol. The cumene layer is withdrawn from the top of extraction tower 48 and passed via line 49 and valve 5| back to extraction tower 8 for separation of the constituents thereof.
The aqueous phenolic layer is withdrawn from extraction tower 48 via line 52 and valve 53, and is introduced into extraction tower 54 for removal of phenol. In extraction tower 54 the aqueous phenol. is countercurrently contacted with a hydrocarbon solvent, suitably benzene. The benzene layer, which contains about 5 or 6% by weight of phenol, is withdrawn from. the top of tower 54 via line 56 and valve 51 and is passed to still 65. The aqueous layer from tower 54, containing about 1% phenol, is recirculated via line 58 and valve 59 to extraction tower 8 where,
together with make-up water introduced via line 6 and valve 62, it serves as the extraction medium for separation of phenol from non-phenolic constituents of the decomposition reaction The phenolic water is likewise passed as needed via line and valve 60 to still I to provide required water in the distilland therein.
In still the hydrocarbon solvent, e. g. benzene, is distilled oil; it is condensed in condenser B3. The condensate is separated into a reflux ward flow stream which is returned to extraction tower 54 via line 66 and valve 61. Make-up hydrocarbon solvent is introduced to extraction tower 54 via line 68 and valve 69.
The phenolic residue from still passes via line H and valve 12 to still 13 wherein phenol is separated overhead. The phenol is condensed in condenser 15 and separated into a product stream, withdrawn via line 14 and valve 16, and. a reflux stream returning to the still via line 11. Bottoms may be withdrawn from still 13 when desired via line 18 and valve 19. Commercially pure phenol is recovered in yields of better than of the phenol originally present in the crude decomposition product.
Conventional items of equipment such as pumps, drains, surge tanks, recording and controlling instruments and so on may be used as desired to control the process above described. These and other modifications and variants o! the above described embodiment of my invention will be obvious to one skilled in the art.
I claim:
1. A process for separating acetone and phenol from a cumene hydroperoxide decomposition mixture containing them which comprises distilling said mixture in presence of water and taking oii acetone overhead; extracting with Water at elevated temperatures of at least about 85 C. phenolic residue of said distillation which residue contains in addition to phenol at least 30% by weight of cumene, with formation of an organic layer and an aqueous phenol layer; neutralizing phenol in the organic layerthus produced and separating aqueous phenol salt solution from said organic layer; extracting from the aforementioned aqueous phenol layer, with cumene solvent, non-phenolic organic impurities therein and combining the organic layer from said extraction with the aforesaid acetone distillation residue; extracting thus purified aqueous phenol with hydrocarbon solvent; separating from organic-extract, thus resulting, hydrocarbon solvent and phenol and recycling aqueous layer, from said extraction of purified phenol, for the aqueous extraction of distillation residue from the acetone distillation step and for providing water in said distillation step.
2. Process as defined in claim 1 wherein the hydrocarbon solvent for extraction of purified phenol from its aqueous solution is benzene.
3. Process as defined in claim 2 wherein a crude acetone-phenol mixture containing about 50 percent by weight of cumene is employed as starting material and the water present in the distilland of the acetone distillation step amounts to about 10 percent by weight of crude starting material introduced for distillation.
GEORGE G. JORIS.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number 1 Name Date 1,595,604 Hefiner et a1 Aug. 10, 1926 2,342,386 Berger et al Feb. 22, 1944 2,357,252 Berger et a1 Aug. 29, 1944 2,368,931 Leum et al Feb. 6, 1945 FOREIGN PATENTS Number Country Date 175,285 Great Britain July 10, 1923

Claims (1)

1. A PROCESS FOR SEPARATING ACETONE AND PHENOL FROM A CUMENE HYDROPEROXIDE DECOMPOSITION MIXTURE CONTAINING THEM WHICH COMPRISES DISTILING SAID MIXTURE IN PRESENCE OF WATER AND TAKING OFF ACETONE OVERHEAD; EXTRACTING WITH WATER AT ELEVATED TEMPERATURES OF AT LEAST ABOUT 85* C. PHENOLIC RESIDUE OF SAID DISTILLATION WHICH RESIDUE CONTAINS IN ADDITION TO PHENOL AT LEAST 30% BY WEIGHT OF ACUMENE, WITH FORMATION OF AN ORGANIC LAYER AND AN AQUEOUS PHENOL LAYER; NEUTRALIZING PHENOL IN THE ORGANIC LAYER THUS PRODUCED AND SEPARATING AQUEOUS PHENOL SALT SOLUTION FROM SAID ORGANIC LAYER; EXTRACTING FROM THE AFOREMENTIONED AQUEOUS PHENOL LAYER, WITH CUMENE SOLVENT, NON-PHENOLIC ORGANIC IMPURITIES THEREIN AND COMBINING THE ORGANIC LAYER FROM SAID EXTRACTION WITH THE ADORESAID ACETONE DISTILLATION RESIDUE; EXTRACTING THUS PURIFIED AQUEOUS PHENOL WITH HYDROCARBON SOLVENT; SEPARATING FROM ORGANIC EXTRACT, THUS RESULTING, HYDROCARBON SOLVENT AND PHENOL AND RECYCLING AQUEOUS LAYER, AQUEOUS EXTRACTION OF DISTILLATION RESUDE FROM AQUEOUS EXTRACTION OF DISTILLATION RESIDUE FROM THE ACETONE DISTILLATION STEP AND FOR PROVIDING WATER IN SAID DISTILLATION STEP.
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Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2679535A (en) * 1952-08-19 1954-05-25 California Research Corp Purification of phenol
US2724001A (en) * 1952-04-19 1955-11-15 Golumbic Calvin Method for the recovery of tar acids by extraction in the presence of an alkali soluble hydrosulfite
US2727074A (en) * 1955-12-13 Phenol
US2744144A (en) * 1956-05-01 Purification of phenol
US2750424A (en) * 1949-06-08 1956-06-12 Hercules Powder Co Ltd Manufacture of cumylphenol
US2794838A (en) * 1952-08-12 1957-06-04 Mora Fernando Mario Continuous process for producing acetone using calcium acetate liquor as starting material
US2824049A (en) * 1958-02-18 Process for the separation of decomposition
US2840515A (en) * 1952-08-12 1958-06-24 Mora Fernando Mario Single circuit process and a plant for producing a series of products using wood as starting material
US2862855A (en) * 1951-11-24 1958-12-02 Ruetgerswerke Ag Azeotrope distillation of aromatic isopropyl compounds from phenol
US2904592A (en) * 1953-07-30 1959-09-15 California Research Corp Production of acetone
US3036882A (en) * 1959-10-29 1962-05-29 Leuna Werke Veb Process for the after-carbonization of alkali-containing phenol oils
US3284506A (en) * 1962-01-10 1966-11-08 Sir Soc Italiana Resine Spa Method of dephenolizing cumene
US3927124A (en) * 1970-03-05 1975-12-16 Goodyear Tire & Rubber Process for the neutralization of alkyl aromatic hydroperoxide rearrangement reaction products
US3968171A (en) * 1970-03-05 1976-07-06 The Goodyear Tire & Rubber Company Process for the continuous isolation of dihydric phenols
US4229596A (en) * 1970-03-05 1980-10-21 The Goodyear Tire & Rubber Company Process for the continuous isolation of dihydric phenols
US4351967A (en) * 1979-11-02 1982-09-28 Mitsui Petrochemical Industries, Ltd. Process for producing phenolic compounds
FR2529196A1 (en) * 1982-06-28 1983-12-30 Lummus Co PURIFICATION OF PHENOL
US4559110A (en) * 1983-07-11 1985-12-17 The Dow Chemical Company Acetophenone recovery and purification
US5344528A (en) * 1993-08-04 1994-09-06 Aristech Chemical Corporation Recovery of phenol from low concentrations with sodium sulfate
US5399776A (en) * 1993-11-24 1995-03-21 The Dow Chemical Company Purification of acetone
US6489518B1 (en) 1999-11-11 2002-12-03 Phenolchemie Gmbh & Co. Kg Process for reducing the salt content of fractions comprising high boilers obtained in the preparation of phenol from cumene, by extraction
WO2014153040A2 (en) * 2013-03-14 2014-09-25 Kellogg Brown & Root Llc Methods and systems for separating acetone and phenol from one another

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB175285A (en) * 1921-02-10 1923-07-10 Posseyer Abwasser Und Wasserre Improvements relating to the removal of phenol and its homologues from waste waters
US1595604A (en) * 1926-01-21 1926-08-10 Rainey Wood Process Corp Treatment of gas liquor
US2342386A (en) * 1941-12-02 1944-02-22 Socony Vacuum Oil Co Inc Process for the recovery of phenols
US2357252A (en) * 1942-01-03 1944-08-29 Socony Vacuum Oil Co Inc Process for the recovery of phenols
US2368931A (en) * 1941-09-30 1945-02-06 Atlantic Refining Co Recovery of phenols from alkaline treating solutions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB175285A (en) * 1921-02-10 1923-07-10 Posseyer Abwasser Und Wasserre Improvements relating to the removal of phenol and its homologues from waste waters
US1595604A (en) * 1926-01-21 1926-08-10 Rainey Wood Process Corp Treatment of gas liquor
US2368931A (en) * 1941-09-30 1945-02-06 Atlantic Refining Co Recovery of phenols from alkaline treating solutions
US2342386A (en) * 1941-12-02 1944-02-22 Socony Vacuum Oil Co Inc Process for the recovery of phenols
US2357252A (en) * 1942-01-03 1944-08-29 Socony Vacuum Oil Co Inc Process for the recovery of phenols

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2727074A (en) * 1955-12-13 Phenol
US2744144A (en) * 1956-05-01 Purification of phenol
US2824049A (en) * 1958-02-18 Process for the separation of decomposition
US2750424A (en) * 1949-06-08 1956-06-12 Hercules Powder Co Ltd Manufacture of cumylphenol
US2862855A (en) * 1951-11-24 1958-12-02 Ruetgerswerke Ag Azeotrope distillation of aromatic isopropyl compounds from phenol
US2724001A (en) * 1952-04-19 1955-11-15 Golumbic Calvin Method for the recovery of tar acids by extraction in the presence of an alkali soluble hydrosulfite
US2794838A (en) * 1952-08-12 1957-06-04 Mora Fernando Mario Continuous process for producing acetone using calcium acetate liquor as starting material
US2840515A (en) * 1952-08-12 1958-06-24 Mora Fernando Mario Single circuit process and a plant for producing a series of products using wood as starting material
US2679535A (en) * 1952-08-19 1954-05-25 California Research Corp Purification of phenol
US2904592A (en) * 1953-07-30 1959-09-15 California Research Corp Production of acetone
US3036882A (en) * 1959-10-29 1962-05-29 Leuna Werke Veb Process for the after-carbonization of alkali-containing phenol oils
US3284506A (en) * 1962-01-10 1966-11-08 Sir Soc Italiana Resine Spa Method of dephenolizing cumene
US3927124A (en) * 1970-03-05 1975-12-16 Goodyear Tire & Rubber Process for the neutralization of alkyl aromatic hydroperoxide rearrangement reaction products
US3968171A (en) * 1970-03-05 1976-07-06 The Goodyear Tire & Rubber Company Process for the continuous isolation of dihydric phenols
US4229596A (en) * 1970-03-05 1980-10-21 The Goodyear Tire & Rubber Company Process for the continuous isolation of dihydric phenols
US4351967A (en) * 1979-11-02 1982-09-28 Mitsui Petrochemical Industries, Ltd. Process for producing phenolic compounds
FR2529196A1 (en) * 1982-06-28 1983-12-30 Lummus Co PURIFICATION OF PHENOL
US4559110A (en) * 1983-07-11 1985-12-17 The Dow Chemical Company Acetophenone recovery and purification
US5344528A (en) * 1993-08-04 1994-09-06 Aristech Chemical Corporation Recovery of phenol from low concentrations with sodium sulfate
WO1995004582A1 (en) * 1993-08-04 1995-02-16 Aristech Chemical Corporation Recovery of phenol from low concentrations with sodium sulfate
US5399776A (en) * 1993-11-24 1995-03-21 The Dow Chemical Company Purification of acetone
US6489518B1 (en) 1999-11-11 2002-12-03 Phenolchemie Gmbh & Co. Kg Process for reducing the salt content of fractions comprising high boilers obtained in the preparation of phenol from cumene, by extraction
WO2014153040A2 (en) * 2013-03-14 2014-09-25 Kellogg Brown & Root Llc Methods and systems for separating acetone and phenol from one another
WO2014153040A3 (en) * 2013-03-14 2014-11-06 Kellogg Brown & Root Llc Methods and systems for separating acetone and phenol from one another
CN105246867B (en) * 2013-03-14 2017-06-13 凯洛格·布朗及鲁特有限公司 For by acetone and phenol method separated from one another

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